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Ask HN: how many years have you "wasted" on failed startups? And any regrets?

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Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#11
Depends how you define 'failed' -- I spent about 20 months (and all my money, and some other people's) on a startup that has ultimately gone nowhere, but has taken me to some fantastic places and will undoubtedly be part of the reason I succeed.

It'll take me another year or so to pay back all that I owe, and to get to financial break-even; and another year or two to save enough to start my next big project, at worst, but that's not stopping me doing stuff on the side, oh no.

Lessons:

Build a product. I turned out to be awesome at selling an idea, and myself, but got too caught up in that to actually execute on a product. I'm only now turning the work I did over that time into something useful to hopefully recoup some of the money, sweat and tears I poured in.

Follow your instinct. (YMMV. I've learnt over the last two years that my instinct is usually spot on, and spending months convincing myself otherwise is entirely fruitless.)

No experiences are ever wasted. Coming to YC to interview (we didn't get in) was absolutely worth it and was part of the reason I've ended up in the Valley.

Pick a landlord who won't mind if you pay your rent a little late.

Pick advisors who understand your business and who understand business itself. Running a web platform startup I had an advisor who had never started his own company and who didn't understand Twitter (a core part of my technology).

People will evangelise you if you impress them. Do it.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#12
I have 20 years of startups. A couple moderately successful...quite a few failed.

Some startups were done more as side projects...and just never got the full dedication.

A couple startups were solo endeavors...quit jobs to run...ran up credit cards.

Still paying 20K from the last one.....

No regrets. Best education I could ever have.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#13
You can't think about things like this. You are, at the core, composed of your history of things that you tried and what you learned doing them.

As I learned here, you cannot give in to regret. You have to pick yourself up and resolve not to make the same mistakes.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#14
I spent probably 6 months to an entire year working on failed or unreleased projects. Some were just little things to learn the language, like a trojan written in VB6 that would do various annoying to the user (like "earthquake" their windows), to a couple of sites I've recently launched that are currently too complicated and/or just not valuable to anybody except me. My outlook at this point is admittedly pessimistic.

Lessons learned, in no particular order, except for the last:

- If you need to explain your app to customers in more than one sentence, or if that sentence contains any four-or-more syllable words, or if any of those words' definitions fail the above two criteria, it will probably fail.

- If you are working on a project to scratch your own itch, confirm that other people have a rash.

- Do not give in to feature creep, unless that feature presents itself immediately and without intervention. For example: Back-end features to improve search results: good. Sliders, filters, color coding, additional search options, menus, extra words, animations, hover effects, etc, will probably only confuse people, unless you are a UX genius, in which case those features will merely go unused.

- People trust their gut instinct on what something does, rather than read instructions, or discover, or wander into unfamiliar territory. Find the design for your product that mimics something people have used to solve a similar problem.

- People are generally incapable of abstraction. If you are the "x of y", that means people need to thoroughly understand x, y, and what it means to abstract one to the other.

- People will exert very little effort into learning something unless the rewards are immediate, have been stated to them by a trusted source, or are made extremely enticing.

- Ideas that require a critical mass of users to be useful are easy to come by, nearly impossible to execute.

- Hope for the best, expect failure.

- Stay the fuck away from anything "meta," or anything involving variables. People like being served things that they pick from a menu, or that people suggest. The most complicated task the average person has to deal with, on any regular basis, is probably choosing multiple toppings for a pizza.

- It is far better to release a crappy implementation of something awesome than it is to release an awesome implementation of something crappy. Awesomeness in the idea is easier and more valuable than awesomeness in the implementation.

- Presentation is much more important than you'd like to believe.

- It is far better to be lucky than any of the above. Yes, you can slightly increase your chances of being "lucky," but don't kid yourself.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#15
post #3

I've burned perhaps a hundred hours on projects which did not go anywhere in the last five years. Actually, I don't like that phrasing. Let me try again: I have spent a hundred hours learning that I have better options than two ideas which seemed like winners until I had done some work on them.

You have only wasted 100 hours in the last five years?!? Holy crap that is awesome efficiency. That is only about 2.5 weeks of going down a fruitless path.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#16
post #6

I've spent most of my adult life in failed startups in some form or another. Some were funded, most were bootstrapped. Probably 6-8 man-years if I subtract my dances with full-time employment (I'm doing contract work now and working on another startup on the side with a partner). I have no regrets. I've asked myself a couple of times if it was worth it, and to be honest I can't think of anything else I would have rat…

Same, I'm still under 30 but have had two startups "fail" over 4 years. The key is finding what you love and I love creating products. Everything I learned in the failures and successes is invaluable: design, development, contract law, outsourcing, marketing, etc. Did I make mistakes, of course but where else can you get that education in just 4 years, and love every minute of it. Now I'm in the process of moving to SF to find a startup to join.

Even in failure I found a market for the technology I developed and came out slightly ahead through creative licensing. The key: never give up. You really find out about yourself when all you have left is your wits. About the companies: The first closed because I was too young and didn't want to move to where I had to, looking back I should have moved. The other failed due to the industry leaders incompetence that endangered human life causing the government to create unforeseen regulations.

PS: Unfamiliar with the area so if anyone knows an awesome startup in SF looking for a product guru who can literally design and develop anything (mobile, consumer electronics, web apps, etc) please let me know.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#17
First startup was a consulting firm when I was 21. I turned freelance clients into a business with a partner. I left my job to focus full time on it for about 6 months burning through savings (I did have a mortgage).

Second startup was a photo sharing startup 3 years later in 2004. We both left our jobs at ClearChannel before we got funding but secured an angel round about 3 months later. That lasted a year and a half before we ran out of money. We made the mistake of rebranding and rewriting the product with the funding (won't do that again). By the time we were ready to market 9 months had gone by and we didn't have a lot of money left.

Currently bootstrapping and looking for when I can leave my day job. We don't have traction yet but I spent 4 weeks hitting the streets and talk to customers (students).

I'm 32 now and after every startup I swear I'm done but I can't not do this. It's in my blood. I apologise to my wife on a regular basis for it. Thankfully she's always been supportive. Two times since we got married 3 years ago and I've looked her in the eyes and said "I think I need to quit my job" twice already.

Hoping the third time is a charm :)

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#18
post #15
post #3

I've burned perhaps a hundred hours on projects which did not go anywhere in the last five years. Actually, I don't like that phrasing. Let me try again: I have spent a hundred hours learning that I have better options than two ideas which seemed like winners until I had done some work on them.

You have only wasted 100 hours in the last five years?!? Holy crap that is awesome efficiency. That is only about 2.5 weeks of going down a fruitless path.

Closer to four months, given how many hours I had to work on my business at the time. It is still cheap at the price, though.

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#19
post #6

I've spent most of my adult life in failed startups in some form or another. Some were funded, most were bootstrapped. Probably 6-8 man-years if I subtract my dances with full-time employment (I'm doing contract work now and working on another startup on the side with a partner). I have no regrets. I've asked myself a couple of times if it was worth it, and to be honest I can't think of anything else I would have rat…

That quote is awesome. I will use that to recruit people in my startup. Thanks quote-source-that-scottw-cant-remember!

Re: Ask HN: how many years have you "wasted" on failed startups? And any regrets?

#20
I "wasted" a year working on projects in a big company that didn't launch. What I realized at the end of it is that doing anything new is doing research. Null results are useful in the sciences, even if they don't make you famous, and null results are useful in product development even if they don't make you rich. You learn from the experience, and if you share your knowledge, the world learns.
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